Impact of the aryl substituent kind and distance from pyrimido[2,1-f]purindiones on the adenosine receptor selectivity and antagonistic properties
Section snippets
Acknowledgements
This study was supported in part by the Polish State Committee for Scientific Research (Grant No 6 P05F 024 21), and by the Deutsche Forschungsgemeinschaft (GRK-677). The authors are grateful to Professor James P. Stables for providing anticonvulsant test data through the Antiepileptic Drug Development Program, National Institutes of Health, Bethesda, Maryland, USA.
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8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors
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1,3-Dialkyl-substituted tetrahydropyrimido[1,2-f]purine-2,4-diones as multiple target drugs for the potential treatment of neurodegenerative diseases
2013, Bioorganic and Medicinal ChemistryCitation Excerpt :Both are widely used as pharmacological tools for in vitro and especially for in vivo studies.33,43,44 We have previously reported on the development of tetrahydropyrimido[2,1-f]purinediones (e.g., compound 9) as AR antagonists, a class of compounds which can be envisaged as tricyclic caffeine derivatives.45–50 They represent analogs of 8-styrylxanthines, that are sterically constrained by anellation of a tetrahydropyrimidine ring to the 7,8-position of caffeine mimicking the (E)-configurated styryl substructure of A2A antagonists 1 and 8.
Synthesis and biological activity of tricyclic cycloalkylimidazo-, pyrimido- and diazepinopurinediones
2011, European Journal of Medicinal ChemistryCitation Excerpt :Therefore, X-ray structure analysis of small, biologically active molecules is highly useful. Previous X-ray studies on imidazo-, pyrimido- and 1,3-diazepino[2,1-f]purinediones with various aromatic substituents in the N-8, N-9 or N-10 position respectively, have suggested that C–H⋯OC interactions are crucial for crystal structure architecture [27–32]. Such H-bonds were mainly formed between the O2 purine oxygen atom and protons from the annelated rings.
Structure-activity relationship studies of a new series of imidazo[2,1-f]purinones as potent and selective A<inf>3</inf> adenosine receptor antagonists
2008, Bioorganic and Medicinal Chemistry